Given you have achieved the means for financial security, I think a more important question to ask yourself instead of "what is the best deal I can get" is "wha

Given you have achieved the means for financial security, I think a more important question to ask yourself instead of "what is the best deal I can get" is "what do I want to build?" You have gotten to where you are by being highly-capable and applying yourself consistently. You have the personal skills and financial leverage to bring about many things in this world. What do you want to build? What needs nurturing the most? What, if any, legacy would I like to leave behind? I believe we are in early days of a century of revolution. Pick your battle and fight it. The money will follow if your work continues to create value. Besides that personal take, it seems like you may not have to make a breaking change. I always try to ask myself "why not both?". Given you're in the tech ecosystem, you probably have an information advantage on what startup investing opportunities exist and which may be viable. There is nothing stopping you from being a part-time angel investor and generating passive income. Certainly you have to source and work deals, but its generally a lot more passive to be a semi-silent partner than one who does it full-time, and as long as you go in with talented investors who want to take a more active role you can be somewhat assured your investment will be shepherded well. Should you find your investment(s) have traction and you feel you can add value with your specific skills, it may make sense to join the team. You can do so while being reasonably assured that you'll average $80K+ / month as a baseline, while also virtually guaranteeing things will be a bit more interesting day to day. Best of luck to you.